WO1998053795B1 - Cosmetic and dermopharmaceutical compositions containing threonine or serine derivatives - Google Patents
Cosmetic and dermopharmaceutical compositions containing threonine or serine derivativesInfo
- Publication number
- WO1998053795B1 WO1998053795B1 PCT/FR1998/000927 FR9800927W WO9853795B1 WO 1998053795 B1 WO1998053795 B1 WO 1998053795B1 FR 9800927 W FR9800927 W FR 9800927W WO 9853795 B1 WO9853795 B1 WO 9853795B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cosmetic
- dermopharmaceutical compositions
- threonine
- compositions according
- acyl
- Prior art date
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract 14
- 239000000203 mixture Substances 0.000 title claims 12
- 150000003354 serine derivatives Chemical class 0.000 title 1
- 150000003587 threonine derivatives Chemical class 0.000 title 1
- 210000003491 Skin Anatomy 0.000 claims abstract 4
- 239000004473 Threonine Substances 0.000 claims abstract 4
- 210000004761 Scalp Anatomy 0.000 claims abstract 2
- 230000037303 wrinkles Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- PEDXUVCGOLSNLQ-WUJLRWPWSA-N N-acetyl-L-threonine Chemical group C[C@@H](O)[C@@H](C(O)=O)NC(C)=O PEDXUVCGOLSNLQ-WUJLRWPWSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 239000006210 lotion Substances 0.000 claims 2
- -1 macro- Substances 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 241000195940 Bryophyta Species 0.000 claims 1
- 108010004103 Chylomicrons Proteins 0.000 claims 1
- 235000010654 Melissa officinalis Nutrition 0.000 claims 1
- 240000004119 Melissa officinalis Species 0.000 claims 1
- 210000004080 Milk Anatomy 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000003862 amino acid derivatives Chemical class 0.000 claims 1
- 125000005418 aryl aryl group Chemical group 0.000 claims 1
- 235000012216 bentonite Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 230000002255 enzymatic Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000000865 liniment Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 239000003094 microcapsule Substances 0.000 claims 1
- 239000011859 microparticle Substances 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 235000011929 mousse Nutrition 0.000 claims 1
- 239000002088 nanocapsule Substances 0.000 claims 1
- 239000002105 nanoparticle Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 229920000620 organic polymer Polymers 0.000 claims 1
- 239000000419 plant extract Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 230000037067 skin hydration Effects 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 230000002194 synthesizing Effects 0.000 claims 1
- 235000012222 talc Nutrition 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 239000007762 w/o emulsion Substances 0.000 claims 1
- 230000036740 Metabolism Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000000887 hydrating Effects 0.000 abstract 1
- 230000001530 keratinolytic Effects 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 230000035786 metabolism Effects 0.000 abstract 1
- 230000004936 stimulating Effects 0.000 abstract 1
Abstract
The invention concerns the novel use of N-acyl-threonine and N-acyl serine derivatives which are β-hydroxylated acids in cosmetics or dermopharmaceutics to accelerate skin renewal, fight against wrinkles, improve general skin and scalp appearance by keratolytic effect, hydrating and/or stimulating the metabolism.
Claims
1. Compositions cosmétiques ou dermopharmaceutiques caractérisées1. Characterized cosmetic or dermopharmaceutical compositions
en ce qu'elles contiennent un ou plusieurs composés quiin that they contain one or more compounds which
correspondent à la formule générale:correspond to the general formula:
CH-ORsCH-ORs
R2 où Ri = alkyl, aryl ou alkylaryl, avec "alkyl" représentant des chaînes carbonées de 2 à 10 carbones, préférentiellement de 2 à 4 carbones, linéaires ou ramifiées, saturées ou insaturées, soufrées ou phosphorylées ou non, R2 = CH3 ou une chaîne alkyle de 2 à 4 atomes carbonés et R3 = H ou une chaîne acyle de 2 à 10 atomes de carbone, préférentiellement de 2 à 4 carbones, et le carbone Cx désigne un atome de carbone asymétrique qui peut être présent dans la forme L, D ou sous forme racémique DL.R 2 where R 1 = alkyl, aryl or alkylaryl, with "alkyl" representing carbon chains of 2 to 10 carbons, preferably 2 to 4 carbons, linear or branched, saturated or unsaturated, sulfur or phosphorylated or not, R 2 = CH 3 or an alkyl chain of 2 to 4 carbon atoms and R 3 = H or an acyl chain of 2 to 10 carbon atoms, preferably 2 to 4 carbons, and the carbon C x denotes an asymmetric carbon atom which may be present in the form L, D or DL racemic form.
2) Compositions cosmétiques ou dermopharmaceutiques selon la revendication 1 caractérisées en ce que les composés objets du présent brevet sont obtenus soit par synthèse organique en milieu homogène ou hétérogène selon les méthodes classiques, soit par synthèse enzymatique en milieu préférentiellement anhydre.2) cosmetic or dermopharmaceutical compositions according to claim 1 characterized in that the compounds of this patent are obtained either by organic synthesis in a homogeneous or heterogeneous medium according to conventional methods, or by enzymatic synthesis in a preferably anhydrous medium.
3) Compositions cosmétiques ou dermopharmaceutiques selon les revendications 1 à 2 caractérisées en ce que les composés choisis sont les N-acyl-thréonine et N-acyl, O-acyl-thréonine.3) cosmetic or dermopharmaceutical compositions according to claims 1 to 2 characterized in that the selected compounds are N-acyl-threonine and N-acyl, O-acyl-threonine.
4) Compositions cosmétiques ou dermopharmaceutiques selon les revendications 1 à 3 caractérisées en ce que le dérivé d'acide aminé β- hydroxylé objets du brevet est la N-acétyl-L-thréonine ou un mélange de N-acétyl-L-thréonine et de N, O-diacétyl-L-thréonine. 5) Compositions cosmétiques ou dermopharmaceutiques caractérisées
1 34) cosmetic or dermopharmaceutical compositions according to claims 1 to 3 characterized in that the β-hydroxylated amino acid derivative of the patent is N-acetyl-L-threonine or a mixture of N-acetyl-L-threonine and N, O-diacetyl-L-threonine. 5) Characterized cosmetic or dermopharmaceutical compositions 1 3
en ce que les composés selon l'une quelconque des revendication 1 à 4 sont préalablement incorporés dans des vecteurs cosmétiques comme les liposomes, les chylomicrons, les macro-, micro- et nanoparticules ainsi que les macro-, micro- et nanocapsules, ou absorbés sur des polymères organiques poudreux, les talcs, bentonites et autres supports minéraux.in that the compounds according to any one of claims 1 to 4 are previously incorporated into cosmetic vectors such as liposomes, chylomicrons, macro-, micro- and nanoparticles as well as macro-, micro- and nanocapsules, or absorbed on powdery organic polymers, talcs, bentonites and other mineral supports.
6) Compositions cosmétiques ou dermopharmaceutiques selon l'une quelconque des revendication 1 à 5 caractérisées en ce qu'elles contiennent le ou les dérivés objets du présent brevet à des concentrations qui peuvent varier entre 0.001 et 30% (p/p), préférentiellement entre 0.1 et 10% (p/p)/ particulièrement avantageusement entre 1 et 5% en poids de la composition totale.6) Cosmetic or dermopharmaceutical compositions according to any one of claims 1 to 5 characterized in that they contain the derivative or derivatives of this patent at concentrations which may vary between 0.001 and 30% (w / w), preferably between 0.1 and 10% (w / w) / particularly preferably between 1 and 5% by weight of the total composition.
7) Compositions cosmétiques ou dermopharmaceutiques selon l'une quelconque des revendication 1 à 6 caractérisées en ce qu'elles représentent toute forme galénique employée en cosmétique ou dermopharmacie à savoir : les émulsions H/E et E/H, laits, lotions, gels, pommades, baumes, mousses, huiles corporelles, lotions capillaires, shampooings, savons, sticks et crayons, sprays.7) Cosmetic or dermopharmaceutical compositions according to any one of Claims 1 to 6, characterized in that they represent any galenic form used in cosmetics or dermopharmacy, namely: O / W and W / O emulsions, milks, lotions, gels, ointments, balms, mousses, body oils, hair lotions, shampoos, soaps, sticks and pencils, sprays.
8) Compositions cosmétiques ou dermopharmaceutiques selon l'une quelconque des revendication 1 à 7 caractérisées en ce que les dérivés objets du présent brevet sont combinés dans les produits finis avec tout autre ingrédient habituellement utilisé en cosmétique ou dermopharmacie: lipides d'extraction et/ ou de synthèse, polymères gélifiants et viscosants, tensioactifs et émulsifiants, principes actifs hydro- ou liposolubles, extraits de plantes, extraits tissulaires, extraits marins.8) cosmetic or dermopharmaceutical compositions according to any one of claims 1 to 7 characterized in that the derivatives of this patent are combined in the finished products with any other ingredient usually used in cosmetics or dermopharmacy: extraction lipids and / or synthetic, gelling and viscosizing polymers, surfactants and emulsifiers, hydro- or liposoluble active ingredients, plant extracts, tissue extracts, marine extracts.
9) Utilisations des composés objets du présent brevet selon l'une quelconque de revendications 1 à 4 dans les compositions cosmétiques ou dermopharmaceutiques selon l'une quelconque des
1 49) Uses of the compounds object of this patent according to any one of claims 1 to 4 in the cosmetic or dermopharmaceutical compositions according to any one of 1 4
revendications 5 à 8 pour les soins de la peau ou du cuir chevelu, particulièrement pour le renouvellement des couches épidermiques, pour améliorer l'hydratation cutanée, pour diminuer les rides et la rugosité de la peau.
claims 5 to 8 for the care of the skin or scalp, particularly for the renewal of the epidermal layers, to improve skin hydration, to reduce wrinkles and roughness of the skin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9706572A FR2763842B1 (en) | 1997-05-27 | 1997-05-27 | COSMETIC OR DERMOPHARMACEUTICAL COMPOSITIONS CONTAINING THREONINE OR SERINE DERIVATIVES |
| FR97/06572 | 1997-05-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998053795A1 WO1998053795A1 (en) | 1998-12-03 |
| WO1998053795B1 true WO1998053795B1 (en) | 1999-02-11 |
Family
ID=9507353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1998/000927 WO1998053795A1 (en) | 1997-05-27 | 1998-05-07 | Cosmetic and dermopharmaceutical compositions containing threonine or serine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2763842B1 (en) |
| WO (1) | WO1998053795A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11279040A (en) * | 1998-03-27 | 1999-10-12 | Kao Corp | Composition for external use for skin |
| EP1908454A1 (en) * | 2005-07-26 | 2008-04-09 | Shiseido Company, Ltd. | Wrinkle-preventive/ameliorating agent |
| HU227970B1 (en) | 2007-07-10 | 2012-07-30 | Egis Gyogyszergyar Nyrt | Pharmaceutical compositions containing silicones of high volatility |
| US10045935B2 (en) | 2012-07-31 | 2018-08-14 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| US11154535B2 (en) | 2012-07-31 | 2021-10-26 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| JP7349076B2 (en) * | 2019-09-26 | 2023-09-22 | 株式会社ファンケル | Melanin production inhibitors and skin whitening agents or skin external preparations containing the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2649697A1 (en) * | 1989-07-11 | 1991-01-18 | Oreal | NOVEL URETHANNE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN PARTICULAR AS MOISTURIZING AGENTS IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF DRY SKINS |
| FR2698869B1 (en) * | 1992-12-09 | 1995-02-24 | Morelle Jean | Acylamino acids obtained from fibers from Bombyx Mori. |
| FR2699169B1 (en) * | 1992-12-16 | 1995-02-03 | Oreal | New primary amine salts derived from amino acids with a urethane group, and their use in cosmetic compositions. |
| US5431904A (en) * | 1993-09-09 | 1995-07-11 | The Gillette Company | O-acyl serines as deodorants |
| FR2719584B1 (en) * | 1994-05-09 | 1996-06-07 | Oreal | New serine derivatives, their preparation and their use in cosmetic or dermatological compositions. |
| TW319797B (en) * | 1994-06-15 | 1997-11-11 | Ajinomoto Kk | |
| US5472698A (en) * | 1994-12-20 | 1995-12-05 | Elizabeth Arden Co., Division Of Conopco, Inc. | Composition for enhancing lipid production in skin |
| FR2732965B1 (en) * | 1995-04-12 | 1997-07-11 | Sochinaz Sa | NEW SERINE DERIVATIVES AND THEIR USE IN COSMETICS |
| FR2738483B1 (en) * | 1995-09-07 | 1997-10-10 | Sederma Sa | NOVEL COSMETIC COMPOSITIONS FOR THE TREATMENT OF HAIR CONTAINING SYNTHETIC LIPIDS |
| WO1998009611A1 (en) * | 1996-09-09 | 1998-03-12 | Societe D'exploitation De Produits Pour Les Industries Chimiques - Seppic | Cosmetic use of compounds with lipoaminoacid structure and cosmetic compositions with soothing activity incorporating some of these compounds |
-
1997
- 1997-05-27 FR FR9706572A patent/FR2763842B1/en not_active Expired - Fee Related
-
1998
- 1998-05-07 WO PCT/FR1998/000927 patent/WO1998053795A1/en active Application Filing
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